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Day 18 · The Prompt SeriesLIVE

Holiday Rental Risk Scanner.

Short-stay rental income looks attractive on paper. Platform dependency, council restrictions, seasonality, and the lender’s refusal to count Airbnb income change the investment case entirely. This prompt stress-tests the numbers before you buy the dream.

Why this matters

Why this matters

The holiday rental listing in a popular coastal town shows peak week income of $4,500. The agent produces an annual projection of $85,000. The property is listed at $980,000. The implied yield is exceptional. The investment case looks compelling.

What the projection doesn’t show is that those peak income weeks represent Christmas, Easter, and two school holiday periods. The 38 weeks outside those windows may produce $300 to $600 per week — or nothing at all in the off-season for a property in a highly seasonal location. The annual income at realistic occupancy is often 30 to 50 percent of the peak-weighted projection.

What the investment case also doesn’t show is that most Australian lenders will not count Airbnb or short-stay rental income in your serviceability assessment at all. You must be able to service this loan on your own income alone, treating every dollar of holiday rental income as a bonus. If you can’t service it without the income, you are taking on significant financial risk that doesn’t appear anywhere in the agent’s pitch.

**Real case study summary:** A buyer purchased a 3-bedroom house in a Mornington Peninsula beach town for $1.1 million based on a projected annual income of $78,000. In year one, actual income was $44,200. The six-week shoulder season had no bookings. The two storm weekends in summer were not included in the projection’s peak figures. The cleaning and management costs were higher than estimated. The mortgage was serviced from personal income throughout — as it would have needed to be regardless. The investment wasn’t a disaster, but it was significantly different from the projected case.

The Airbnb income in the listing is the best week of the year. The investment has to survive the rest of them.

What you're building

What you're building

The end result

A short-stay holiday rental cash flow stress-test outlining: seasonal occupancy models (peak, shoulder, off-season), cleaning and platform management costs, postcode-specific short-stay restrictions, and lender income exclusions.

What you need

Claude (free tier works), purchase price, peak weekly Airbnb rental rate, management commission fee, and local council short-stay regulations.

Step 18

Copy the prompt.Paste your details.Analyze the output.

Paste the prompt below into Claude or ChatGPT. Replace the bracketed fields with your specific property or portfolio details.

i.Open Claude at claude.ai or ChatGPT at chatgpt.com. Free tier works fine for this prompt.Browser
ii.Copy the full Day 18 prompt below and paste it into a fresh chat.Chat
iii.Replace the bracketed details with your actual property and financial information.Edit
iv.Send. Read the structured output sections carefully.Output
Done. The structured analysis is in front of you.
Heads up

Always verify the AI's assumptions with qualified professionals. This output is a first-pass educational tool, not advice.

01
The Prompt

Holiday rental test

Short-stay and Airbnb cash flow stress-test · seasonal vacancy model

Copy & Paste
You are an Australian property research assistant helping a buyer assess the real risks of a holiday rental investment before purchase. The numbers in listings and agent projections for holiday rental income are almost always optimistic. Help me see the full picture.

PROPERTY DETAILS:
- Location: [suburb, town, state]
- Property type: [house / apartment / unit / cabin / other]
- Asking price: $[amount]
- Configuration: [bedrooms, bathrooms, sleeps how many]
- Proximity to tourist attraction or beach: [walking distance / driving distance — how far]
- Current use: [already operating as short-stay / currently long-term rental / currently owner-occupied / vacant]
- Income claimed by agent or vendor: $[X per year or $X per week in peak season]

MY INTENT:
- I plan to use it myself: [yes — approximately X weeks per year / no]
- I will manage it: [myself / through a local agency / through Airbnb or Stayz only]
- I intend to keep it long-term: [yes / sell after X years]
- My primary return expectation: [capital growth / rental income / combination]
- Will I need this property to be positively cash-flow neutral or positive? [yes / no / preferred but not essential]

Return a holiday rental risk assessment with these 7 sections:

## 1. THE INCOME REALITY CHECK
This is the section that should come before any other analysis.
- Peak season versus annual income: the income figure in most holiday rental listings represents the property's best weeks of the year — Christmas, Easter, school holidays, major events. Describe what occupancy rates typically look like outside peak season in this type of location.
- Realistic occupancy rate: for a [location type] holiday destination, what is a realistic annual occupancy rate? Describe the range from optimistic to conservative.
- Apply my stated income claim: if the agent says $[X per year], what occupancy rate does that imply? Is that realistic?
- Conservative income estimate: at a conservative occupancy rate of X%, what annual income can I realistically expect?
- Platform fees: Airbnb typically charges 3% to the host; Stayz and similar platforms vary. Management agency fees for holiday rentals are typically 15–25% of gross income — note how this differs from standard long-term property management at 7–9%.
- Net income after platform fees and management: calculate what I actually receive.

## 2. COUNCIL AND REGULATION RISK
Short-stay regulation is one of the fastest-changing areas of Australian property law.
- My state's current short-stay regulation framework: describe the current rules for short-stay accommodation in my state
- Local council restrictions: some councils have banned or severely restricted short-stay accommodation, particularly in strata buildings and high-density zones. Flag whether this is a risk for my location and property type.
- Strata by-law restrictions: if this is an apartment or unit, some strata corporations have passed by-laws prohibiting short-stay letting. Describe how to check and verify this.
- State government code of conduct and compliance: describe the registration requirements, noise and behaviour complaints processes, and neighbour relations risks in my state.
- Future regulation risk: short-stay accommodation regulation is tightening in most Australian states. This is a material risk to any holiday rental investment strategy — what I am legally permitted to do today may change.

## 3. THE LENDER'S POSITION ON HOLIDAY RENTAL INCOME
- Will my lender count holiday rental income for serviceability? Almost certainly not at full value, and many lenders do not count it at all. Describe the lender landscape for short-stay income.
- If lenders won't count the income, how do I qualify? I must be able to service the loan on my own income alone, treating the holiday rental income as a bonus rather than a requirement.
- LVR restrictions: some lenders restrict LVR for properties in known holiday or resort postcodes. Flag whether my location is at risk of this restriction.
- Flag: verify with a mortgage broker that you can service this loan without counting a single dollar of holiday rental income. If you cannot, you are taking on significant financial risk.

## 4. THE CASH FLOW MODEL — HONEST VERSION
Run the numbers honestly:
- Annual gross income (conservative occupancy): $[calculate]
- Less: platform commission at X%: $[calculate]
- Less: management fees at X%: $[calculate]
- Less: cleaning costs per turnover × estimated turnovers per year: $[estimate]
- Less: linen, consumables, maintenance, and replacement items: $[estimate — typically $X per booking night or $X per year]
- Less: council rates: $[estimate]
- Less: insurance (holiday rental insurance is more expensive than standard landlord insurance): $[estimate]
- Less: mortgage repayments (interest only at current rate): $[calculate]
- Net annual cash flow: $[calculate]
- Am I cash flow positive, neutral, or negative at conservative occupancy?
- At what occupancy rate do I break even?

## 5. THE THREE RISKS MOST HOLIDAY RENTAL BUYERS UNDERESTIMATE
Based on my property location and type, describe the three most relevant risks from this list in detail:
- Regulation change: the platform may be restricted or banned by council or state government
- Platform dependency: a large portion of income depends on Airbnb or Stayz — platform policy changes, algorithm changes, or a competitor can change your income overnight
- Seasonality trap: in some locations, 80% of revenue is earned in 12 weeks. The other 40 weeks carry full costs with minimal income.
- Neighbour and body corporate conflict: short-stay guests create more noise, wear, and conflict than long-term tenants. Body corporates are increasingly passing restrictions.
- Capital growth risk: many holiday markets are driven by lifestyle rather than population, which makes capital growth less reliable than metropolitan markets

## 6. MY BREAK-EVEN AND EXIT ANALYSIS
- At what point does this property pay for itself on an annual cash flow basis?
- If I need to switch to long-term rental: what would this property achieve as a standard long-term rental? How does that compare to the holiday rental income I am projecting?
- Exit market: when I sell, who are the likely buyers? Is the buyer pool for holiday rental properties in this location deep enough to support a sale at a reasonable price within a reasonable timeframe?

## 7. WHAT TO VERIFY BEFORE SIGNING
Generate a 10-item verification checklist specifically for a holiday rental purchase in my location. Include who I should speak to for each item.

---
Educational analysis only. Not financial, legal, or investment advice. Holiday rental income, local regulation, and lender policies change frequently. Verify all assumptions with a local property manager, the relevant council planning department, a specialist mortgage broker, and a property lawyer before making any holiday rental investment decision.
Run before buying a holiday rental. Ensure you can service debt without Airbnb income.
A real run
Case Study

A buyer purchased a 3-bedroom house in a Mornington Peninsula beach town for $1.1 million based on a projected annual income of $78,000. In year one, actual income was $44,200. The six-week shoulder season had no bookings. The two storm weekends in summer were not included in the projection’s peak figures. The cleaning and management costs were higher than estimated. The mortgage was serviced from personal income throughout — as it would have needed to be regardless. The investment wasn’t a disaster, but it was significantly different from the projected case.

Step 04 · Refine

Your first run is fine. Your fifth is sharp.

Tune 01

Stress-test highly seasonal occupancy

Run the model with 40%, 50%, and 60% occupancy rates to see how winter bookings affect your holding costs.

Tune 02

Exclude short-stay income from borrowing capacity

Verify that you can service the loan using only standard long-term lease rent assumptions or your personal income.

Tune 03

Factor in local council Airbnb levies

Add specific local holiday rental licensing fees and surcharges, as these regulations tighten across Australia.

Save it

Save this holiday rental scanner in your Claude Project. Re-run it before buying in any tourist-dependent market.

The honest bit

What it still gets wrong.

i.

Holiday rental occupancy is seasonal

Peak occupancy is limited to school holidays and summers. Off-season weeks often yield zero income, creating severe cash flow fluctuations.

ii.

Lenders exclude short-stay income

Most banks will not count Airbnb or short-stay income in borrowing capacity, requiring you to service the loan from personal income.

iii.

Higher management commissions

Holiday rental managers charge 15-25% of gross bookings, compared to 7-8% for standard residential property managers.

iv.

Council and state regulations tighten

Many Australian councils are introducing Airbnb registration fees, cap limits on booking nights, and commercial rates.

The Workflow

How this stacks.

Day 18 stress-tests Airbnb yields. Day 04 stress-tests standard cash flow. Day 10 scans regional postcode limits. Stack them to verify holiday returns.

The week three vision

Before you buy a holiday home.

You'll have modeled realistic seasonal occupancy and management costs.

You'll know if the property can service its debt on standard rental rates when holiday bookings are slow, and check if your lender excludes Airbnb income.

Coming next
19
Day 19 · live now

Climate risk scanner

Insurance availability and climate risk check · hazard zone overlay

Read Day 19